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Tandem Wittig Rearrangement/Aldol Reactions for the Synthesis of Glycolate Aldols

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journal contribution
posted on 28.09.2006, 00:00 by Myra Beaudoin Bertrand, John P. Wolfe
A new tandem Wittig Rearrangement/aldol reaction of O-benzyl or O-allyl glycolate esters is described. This reaction generates two carbon−carbon bonds and two contiguous stereocenters in a single step from simple starting materials. The [1,2]-Wittig rearrangement proceeds under very mild reaction conditions that do not require the use of a strong base, and the 1,2-diol products are obtained in good yield with excellent diastereoselectivity (>20:1).

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